


That Kind of Bear

by angelofthequeers



Category: Supernatural
Genre: Angst, Bad Matchmaking, Bad Pick-Up Lines, Bisexual Dean Winchester, Bisexual Sam Winchester, Chubby Dean Winchester, Dean Has Self-Esteem Issues, Dean has anxiety, Fluff, Hint of Stucky if you squint, Human AU, It's just kind of embarrassing for Dean, M/M, Misunderstandings, Romance, Shit it's not actually as angsty as I make it sound
Language: English
Status: Completed
Published: 2018-07-15
Updated: 2018-07-15
Packaged: 2019-06-10 21:24:22
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,228
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15300321
Author URL: https://archiveofourown.org/users/angelofthequeers/pseuds/angelofthequeers
Summary: Dean likes Cas. Dean loses a bet to Charlie. His punishment? Use the shittiest pick-up line in existence to ask Cas out. Good thing he likes crappy rom coms so much because his life just became one.





	That Kind of Bear

**Author's Note:**

> Disclaimer: I don’t own SPN.
> 
> Goddammit Facebook, interrupting my mad hyperfixation on a video game with inspiration for a Destiel fic. But I suppose I do need to start writing again, sooooo…
> 
> Also, I basically took my own embarrassed feelings of being rejected after taking a risk and asking out a guy and amplified them, so this is probably just a huge barrel of cringe. And Dean's not actually a twink like in the original, since he's a chubby baby teddy instead of youthfully slim, but I've found myself loving chubby Dean a lot so that's what I went with.
> 
>  
> 
> [Original source here.](https://twitter.com/trans_tho/status/1017451678948356096)

“No way,” Dean said immediately. “No fucking way –”

“You lost the bet!” Sam was far more damn gleeful than a sixteen-year-old had the right to be, practically bouncing on his heels. “You have to do it!”

“I’ll literally eat your disgusting kale salad shit for a whole year if I have to,” Dean said desperately. “Please, Sam, don’t make me do this. I’ll even be your personal slave.”

“Hey, if it was just me, I’d take you up on that in a heartbeat,” Sam shrugged. “But Charlie _knows_.”

Dean shuddered. When Charlie _knew_ , there was quite literally a negative chance of ever getting out of something if she didn’t want you to. And Dean knew that his best friend would sooner make out with him than let him wriggle out of this, which would never happen since she was gay and pretty much the sister he never had.

“If it was anyone but Cas –” he started.

“Then she wouldn’t even have thought of this,” Sam said. “But I’ll give her points for originality. I don’t think this pick-up line’s ever been used before.”

“But he’s _not_ a bear!” Dean said. “I mean, yeah, he’s got the hot muscles going on –”

“Gross.”

“– but he’s not built like a fuckin’ brick house! And he’s probably not hairy enough anyway.”

“Again, gross.”

“Oh, come on. You’re as bi as me, bitch,” Dean said. Sam rolled his eyes.

“Yeah but bears aren’t my type, jerk.”

“Look, can’t you just – I dunno – tell her that I did it?”

“And risk her finding out that I lied?” Sam’s eyes widened comically. “Then she’ll do something to _me_!”

Dean whined and rocked on the balls of his feet, trying to resist the urge to clutch at his violently fluttering belly. He already looked like a creep, lurking outside this store with his brother, so he didn’t need to look even more suspicious than he already did.

“If it makes you feel any better,” Sam said, “I’ll buy you pie as a reward after this.”

Dean perked up ever so slightly at that. “A _whole_ pie?”

“Apple,” Sam said. “I’ll even buy two. Celebration if he says yes, consolation if he says no. Which he won’t. Anna never shuts up about how much this guy talks about you. I even had to spend five minutes listening to the finer points of my brother’s ass, which is _not_ something I ever wanted to hear.”

Dean bit his lip, staring at the store while picking at the hem of his _Led Zeppelin_ shirt. He didn’t have a choice anyway, what with Charlie’s single-minded determination to play matchmaker, so the bribe of pie was just the push he needed. Hey, if he completely flopped and couldn’t look his acquaintance-in-mall-passing slash crush-of-three-years in the eye ever again, at least he’d have comfort pie. And he’d also have the bitter satisfaction of rubbing it in Charlie’s face and telling her to butt out of his business and quit trying to act like she knew what was best. As much as he loved his best friend, her lack of boundaries really did get on his nerves sometimes.

“Fine,” he forced out. “God, what happened to just walking up and winking and getting them to fall at my feet?”

Sam just rolled his eyes and shoved Dean towards the store. “Go on, Dean. Go do what Charlie said. Think of the pie!”

Dean swallowed, ran a hand through his hair, then cleared his throat and allowed his natural flirty smile to wriggle out of hiding and spread across his face. With one last bitchface over his shoulder at Sam, he sauntered into the bright Build-A-Bear store and his heart promptly leapt into his throat at the sight of the man behind the counter talking to a small girl. Cas was unfairly gorgeous normally, with his messy black hair and bright blue eyes and lithe but toned body, but he was so unfairly beautiful with a smile lighting up his face as he talked to the girl that Dean would’ve thanked him profusely for kicking him in the gut. Which was probably going to happen right now, honestly.

When the girl left – because Dean wasn’t a fucking masochist – Cas’ gaze swept around the store for more customers and landed on Dean, who seemed to be the only other person around.

“Can I help you?” Cas said in a rather generic customer service voice. Well, that was just a great start. Dean swallowed, taking a moment to wipe his sweaty palms on his jeans while making sure to never stop smiling, then recited the line that Charlie had fed him.

“Hi, I’d like him to be six foot at least, hairy – obviously – strong but can be chubby, a big d–”

“Sorry, I think you have the wrong idea about what we do here,” Cas interrupted, his cheeks reddening. Dean stopped dead in his tracks. The plan had been to rattle off certain attributes jokingly, then pretend that he’d messed up and proceed to list Cas’ attributes – and if he was on the receiving end then he’d honestly have seen the humour in it – but a flat-out rejection before he could even finish immediately deflated him.

“Oh – I – never mind.” Dean turned and hightailed it out of there before Cas could say anything else. Outside, Sam opened his mouth to say something, but Dean just stalked past without a word, trying to ignore how his heart hammered in his ears and his insides twisted nauseatingly.

That was the last fucking time he took Charlie’s advice regarding anything.

* * *

 

“Dean, this is getting ridiculous!”

“You’re ridiculous!” Dean retorted at his bedroom door through a mouthful of pity pie. On his laptop screen, Bucky and a bloody Cap were currently having their heartfelt ‘beat you up until you say meaningful words to make me remember what you mean to me’ moment, but it was kind of hard to pay attention to the movie with a jerk younger brother outside and a big pile of self-pity inside.

“It’s been a week, Dean! I’ve never seen you mope over a rejection this long! You got over Cassie Robinson in a few –”

“Yeah, ‘cause she outright said no!” Dean shoved another large piece of pie in his mouth. “And I just straight-up asked her out – I didn’t come at her with some shitty line that Charlie fed me! But Cas – he didn’t just stop me, he shut me right down. Not that your geeky ass would have any idea how embarrassing that is when you can’t even talk to Jess.”

Sam was silent for a moment. “That’s not fair, Dean,” he said quietly, voice muffled by the door between them. With a loud sigh, Dean untangled himself from his nest of avoidance and unlocked his bedroom door to let Sam in because damn it, the kid was right. That was totally uncalled for, no matter how much Dean was wallowing.

“And I didn’t have a goddamn huge crush on her for three years,” Dean said, burying himself in his nest again. Sam had the sense to sit down at Dean’s desk rather than try and disturb the pity nest on the bed. “Not only that but I gotta see Cas every damn time I go to work, so I can’t even hide away till I get over it. Kinda hard to avoid the guy when you work in the same part of the same mall. As if pretending to give a fuck while I give out greasy food isn’t bad enough.”

“And he doesn’t talk to you?” Sam said.

“The fuck do you think, Sam? No, he just does that thing where he doesn’t look you in the eye but you can tell he’s watching you. Did Anna say anything to you about him?”

“Just that Cas has been quieter than usual,” Sam shrugged. “I think Cas thought you were being an ass because he used to only get asked out as a joke, remember?”

Oh yeah, Dean definitely remembered their high school days. Hell, that was why he hadn’t tried to ask Cas out then, because the last thing he needed was for the guy to think he was just fucking with him like every other person. Nice to know that he’d turned out precisely like all those assholes.

“I tried explaining that you really meant it, but I don’t think Cas took me seriously. He probably thinks I’m just sticking up for my brother.”

Dean groaned and buried his face in his pillow, weighing up the pros and cons of suffocating himself then and there. He wouldn’t ever have to face Cas again, but Sam probably wouldn’t let him get away with self-imposed asphyxiation two feet away, so there wasn’t any point.

“Are you ever going to talk to Charlie again?” Sam said. “She feels really bad, you know. She genuinely thought it’d be funny, not humiliating.”

“Charlie made this mess, she can damn well fix it,” Dean said into the pillow. Sam didn’t say anything to that, and it wasn’t until he heard the sound of Sam’s footsteps out of the room that Dean emerged from his pity nest to lock himself away again and then rewind the end of the movie.

* * *

 

“Dean, I know you’re mad at me, but can you just come out here for two seconds?” Charlie called a few hours later. Dean just scowled and focused on the new movie with a burning determination to not listen to his best friend. Yeah, he loved Charlie to bits, but he’d always hated that trope of best friends sticking their nose in and playing matchmaker to force two people together. If he hadn’t lost that damn bet in the first place, he’d never have let himself be roped into that situation. So he was going to let her stew for a little while longer before forgiving her and then working on not feeling like a total dickhead every time he saw Cas.

“I know you’re ignoring me and I’d normally say you’re justified and leave you alone but Dean, you have to come out here! Please? I swear you won’t regret it.”

“You gonna bet on that too?” Dean snapped back. Charlie’s silence made a seed of guilt bloom in Dean’s gut, but he resolutely ignored it. Guilt or not, he was the one who had to live with the humiliation of being a douchey asshole, not Charlie.

Okay, so maybe he was being just a _little_ dramatic. It wasn’t as though Dean had never been called a drama queen before, after all. Combining that with constant anxiety and an unhealthy tendency to avoid his problems rather than face them like a mature, functioning adult made up the building blocks of Dean Winchester.

“I’m sorry, okay?” Charlie said. “I know you’ve had a thing for Cas for, like, three years now, and I totally love Gilda to bits and, I dunno, I just get upset for you, so I wanted to fix it and –”

During Charlie’s speech, Dean staggered from the bed to the door and opened it to confront her, if only to prevent her from suffocating herself by forgetting to breathe as she talked. Opening the door in her face was enough to stun Charlie into silence, which thankfully resulted in her actually breathing and not passing out from lack of oxygen.

“You know how much I hate that matchmaker shit,” Dean said. “You can’t seriously say you thought it’d work after all those shitty chick flicks you’ve made me watch?”

“Okay, for one, you actually like shitty chick flicks,” Charlie said. “You can’t lie to me, Winchester, I’ve seen you bawling your eyes out. And two, I’ve also read enough fanfiction to know that it always works out in the end, so I figured we might be lucky?”

“This isn’t a fanfiction, Charlie.” Dean rolled his eyes. “Can I go back to sulking now?”

“I know, I know! I messed up. And I totally forgot about your anxiety. But in my defence, you can flirt like a boss, you know?”

“Yeah, when the person’s not Cas and I don’t have to use some shitty pick-up line my best friend fed me,” Dean said. Charlie winced.

“Okay, that’s totally fair. I deserve that. Look, just come with me, okay?”

“No. I’m gonna go mope again ‘cause Mom’s gonna drag me out for dinner later tonight, so I wanna make sure I mope enough before then.”

“Seriously, Dean, I promise that it’s actually good this time.” Charlie reached out to grab his wrist, being one of the only people who could get away with that without getting punched. “Like, I actually talked to people. No misunderstandings here.”

“If I do then will you leave me alone to sulk?” Dean sighed. When Charlie wanted something, Charlie got it.

“Oh, trust me, you won’t be sulking after this,” Charlie said. “But sure, if that’s what you want. Come on!”

Though he was certain this was the worst idea in the history of bad ideas, Dean reluctantly allowed Charlie to lead him down the stairs and through the double doors into the living room. Not two seconds after entering, he froze where he stood, heart leaping into his throat.

“Hello, Dean,” Cas said. The annoyingly gorgeous asshole was in _his_ living room. _Smiling_. What the fuck was Charlie’s deal?

“Uh – hi,” Dean managed to croak. His palms were starting to grow sweaty, so he wiped them on his pants, then came to the chilling realisation that while Cas was dressed in a beige trench coat, a T-shirt, and jeans that clung to his body, Dean was wearing a faded, oversized shirt speckled with pie crumbs and a pair of grey sweatpants. For Christ’s sake, one of the pant legs was rolled up to his knees from the sheer amount of time he’d spent rolling over in his bed!

Charlie was so fucking dead.

“Excuse me for the next thousand years,” Dean blurted out, turning to bolt from the room and hide in his bed again. But the living room doors were shut, so it was all he could do to not smack into them and make even more of an idiot of himself. Great. Now he was stuck in his own living room with the guy he’d made a dick of himself around, dressed in the sloppiest lazy clothes and probably with pie around his mouth. It wouldn’t be so bad if it was just another rejection instead of Dean being shut down in the middle of a shitty line, because now he just looked like a sleazy douche.

“Charlie explained everything to me,” Cas said. “I didn’t believe Sam, but Charlie confirmed everything he said. She said that she won a bet and made you ask me out with that awful line, but that you were just using it for a joke and didn’t actually mean it.”

“Right. Yeah. Didn’t mean it.” Dean gave a nervous little laugh, still not turning around to face Cas because there was no way he could handle that. “You try saying no to Charlie when she wins a bet.”

“She seems very…forceful,” Cas agreed. They lapsed into the most painful silence that Dean had ever experienced. Dear god, why couldn’t he just go upstairs and die for a few hours?

“Well, I’m actually right in the middle of _Iron Man_ ,” Dean said with an awkward laugh. “So yeah, sorry about the shit, I didn’t mean to be an ass –”

“ _Iron Man_?” Cas said. “The first one, right? I’m not a huge fan of the next two.”

“Look, you don’t have to be all nice,” Dean said quickly, his words falling over themselves. Better to get this out of the way as quickly as possible, like ripping off a band-aid. “I’m sorry, you get it, it was just all a mistake, I didn’t mean it –”

“Charlie gave me the impression that you did mean to ask me out,” Cas said. “And that it was just the method you didn’t mean. I thought getting to know someone was a date essential.”

If Dean’s heart beat any faster, he was going to have a heart attack on the spot. “W-What? I don’t – a date –”

“I didn’t think you were interested, and I thought you were just being mean like everyone else the other day,” Cas said. “I’m glad you actually meant it. And this isn’t a very conventional way to hopefully go out with someone, but I think it’s funny in a way. It would certainly give us a story to tell if we did decide to date.”

Hands shaking like mad, Dean turned to gauge Cas and see if the other guy was just trying to turn it back on him and get back at him for being an asshole. But no, Cas was actually smiling and looked like he was serious and Christ, Dean was about to pass out from the overwhelming anxiety.

“Y-You don’t want me,” he said hoarsely. “I look like fucking trash.”

“You look comfortable,” Cas countered calmly.

“I’m a fat shit.”

“You look more chubby to me. And I like thicker people. That just means there’s more for me to use as a pillow.”

“I eat like a pig. I’ve probably got pie all over my mouth.”

“You don’t, but I still wouldn’t mind if you did.”

“But I –”

“Dean, I think we’ve already established that we have a mutual attraction,” Cas said, looking rather amused. “You can stop putting yourself down to try and repulse me. Actually, I’d like to know if you’d be willing to go out on a date with me.”

“How long’d it take you to work up the courage to do that?” Dean said, letting out a hoarse laugh.

“About five years,” Cas said with a nervous little smile. “But you were so handsome and popular and there was no way you could want the weird, asocial nerd.”

“I’m a fuckin’ train wreck of anxiety and issues who burned out and was too dumb to go to college and still lives with his parents, but sure, let’s go with handsome and popular.”

“If you say yes, you can stop right there with the self-deprecation.” Cas crossed his arms.

“Damn it, and I was gonna say yes,” Dean joked weakly. His insides fluttered something fierce when Cas laughed at that. “Fine, whatever. You win. When d’you wanna do this?”

“How about tomorrow night at seven?” Cas said. “You’ll have to pick me up, since I don’t have a car. I live close enough to the mall that I can get by without one.”

“Okay, sure, seven it is. Uh…see you then.”

“Dean,” Cas said when Dean turned to wrench open the doors and hide his jittery sack of meat under the covers for the next twenty-four hours. “You’ll need my address, right?”

“Right – yeah.” Dean managed to hold it together just long enough for Cas to give an address and then leave, then he collapsed onto the couch and made a strange sound into the cushion.

“See? I said you wouldn’t regret it!” Charlie’s voice said suddenly. Where she’d come from, Dean had no idea, but he’d given up questioning it a long time ago. “Am I forgiven yet?”

Dean just whined into the cushion, wondering what the hell he’d gotten himself into.


End file.
